How to deal with “shit” as a CEO — strategies for managing your psychology

“Psychology is the most under-appreciated, yet most important part of building a company.”

Building an important company over time has a lot to do with product, capital, team and market.

It has more to do, however, with what you (the CEO) tell yourself every day during those “internal conversations” that play out in your head.

CEO psychology is the most under-appreciated, yet most important part of building a company. It rarely gets any attention because it’s not “sexy”. But man is it important.

Everyone talks about startups being akin to rollercoaster rides. There are high highs and low lows. The highs are easy to deal with — you celebrate with your team, share the victories with your friends and partner and maybe even down a few beers that night.

What’s harder to deal with are the (seemingly constant) lows — when things don’t work out as you expect them to. Examples include having an important employee resign, a potential investor pulling a term sheet at the last minute, a competitor winning a big partnership deal and employees passing away.

All of these have happened to me at some point in the last 10 years. And the only way through all the shit is to make sure you talk to yourself every day — but in the right way. Not out loud, of course, but in your head.

There are also certain ways you can look at problems to quickly figure out if they’re potential “company killers” or if they’re just bumps along the way.

As a CEO, you need to find constant inspiration and rationale to move forward. That’s what I’m hoping to give you in this post.

Here are some “no bullshit” ways to manage your psychology as a CEO. Everything here comes from my direct experience over the last decade or so building Bigcommerce ($10B in orders, 100,000 customers, 500 employees, $125M in VC) and a few other companies.

1. Use best/worst/probable analysis when weighing decisions

Most things we fear never materialize, but we spend so much time stressing over the “what ifs”. An alternate approach is to look at decisions and problems rationally by creating a best/worst/probable case analysis.

It’s easy to do — create a spreadsheet with the following columns:

Outcome

Chance (%)

Stop

Start

Keep Doing

… then fill in the spreadsheet with 3 outcomes:

Best outcome

Worst outcome

Probable outcome

Chance (%) is the chance of that outcome happening. It’s a percentage from 1 to 100. In the “stop” column, list the things you’d stop doing if that outcome came to fruition. In the “start” column, list things you’d start doing if that outcome came to fruition. In the “Keep Doing” column, list things you’d keep doing if that outcome came to fruition.

Pretty simple stuff, but writing down each possible outcome and looking at things objectively and rationally can help get the negative, fearful thoughts out of your head extremely quickly, especially when you realize the chance of the worst outcome actually happening is probably tiny.

2. Focus like crazy to make meaningful progress

Progress beats the crap out of fear. Every. Single. Time.

If you feel like shit, commit to spending the next 24 or 48 hours working your ass off to make meaningful progress on something that’s important to you — and it does NOT have to be about your business.

You could run 10 miles each day, spend more time with your partner, design a new product, write a 10,000 word blog post. Whatever it is, make sure the effort is rewarded with a legitimate feeling of progress in some area of your professional or personal life.

Feeling like things aren’t moving as quickly as they should be is the entrepreneur’s curse. You always want things to move faster and it’s easy to get frustrated when they don’t.

3. Know when to step away

Some days you’ll just feel down. It happens to everyone. On those days, don’t go into the office. Cancel your meetings. Spend time alone and do whatever takes your mind off things. Read, write, exercise, play video games. It doesn’t matter.

One big key to maturing as an entrepreneur is to know when you’re just not up to working as you normally would. It might be one day every month or one day every year. But tune in to your thoughts and feelings and don’t fight them. When you’re forcing yourself to work, it’s time to do the opposite.